5-((2,3-dibromo-4,5-dihydroxybenzyloxy)methyl)-3,4-dibromobenzene-1,2-diol | 74849-07-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-((2,3-dibromo-4,5-dihydroxybenzyloxy)methyl)-3,4-dibromobenzene-1,2-diol
• 英文别名: 3-bromo-4-(2,3-dibromo-4,5-dihydroxybenzyl)-5-methoxymethylpyrocatechol；bis(2,3-dibromo-4,5-dihydroxylbenzyl) ether；bis(2,3-dibromo-4,5-dihydroxybenzyl) ether；bis(2,3-dibromo-4,5-dihydroxybenzyl)ether；3,4-dibromo-5-[(2,3-dibromo-4,5-dihydroxyphenyl)methoxymethyl]benzene-1,2-diol
• CAS: 74849-07-3
• 化学式: C₁₄H₁₀Br₄O₅
• 分子量: 577.846
• InChiKey: NVINDBOUFPDPNZ-UHFFFAOYSA-N

物化性质

• 熔点：
  180-182 °C
• 沸点：
  594.9±45.0 °C(Predicted)
• 密度：
  2.332±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  90.2
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-溴香兰素 在 sodium tetrahydroborate 、 溴 、 三溴化硼 、 potassium carbonate 、 三乙胺 、 对甲苯磺酰氯 作用下， 以 甲醇 、 二氯甲烷 、 溶剂黄146 、 乙腈 为溶剂， 反应 4.0h， 生成 5-((2,3-dibromo-4,5-dihydroxybenzyloxy)methyl)-3,4-dibromobenzene-1,2-diol
  参考文献：
  名称：

  Synthesis and α-Glucosidase Inhibitory Mechanisms of Bis(2,3-dibromo-4,5-dihydroxybenzyl) Ether, a Potential Marine Bromophenol α-Glucosidase Inhibitor

  摘要：

  从海藻中提取的双（2,3-二溴-4,5-二羟基苄基）醚（BDDE）是一种潜在的α-葡萄糖苷酶抑制剂，可用于治疗 2 型糖尿病。在本研究中，建立了一条获得 BDDE 的有效合成路线。研究采用荧光光谱、圆二色光谱和分子对接等方法阐明了BDDE对α-葡萄糖苷酶的抑制机制。结果表明，利用已有的合成方法可以有效、高效地制备 BDDE。合成的BDDE与α-葡萄糖苷酶结合，并诱导该酶发生微小的构象变化。对接结果表明，BDDE 与 α-葡萄糖苷酶之间的相互作用是由疏水作用力和氢键共同驱动的。对接的BDDE分子完全埋藏在α-葡萄糖苷酶的结合袋中，部分分子到达催化中心并与葡萄糖的位置重叠，其余分子向蛋白质表面延伸。这项研究为了解 BDDE 与α-葡萄糖苷酶的相互作用以及开发新型α-葡萄糖苷酶抑制剂提供了有用的信息。

  DOI：

  10.3390/md9091554

文献信息

• Bromophenols as Candida albicans isocitrate lyase inhibitors
  作者：Ki-Bong Oh、Heung Bae Jeon、Yu-Ri Han、Yeon-Ju Lee、Jiyoung Park、So-Hyoung Lee、Dongsik Yang、Mihyun Kwon、Jongheon Shin、Hyi-Seung Lee

  DOI：10.1016/j.bmcl.2010.09.015

  日期：2010.11

  A new series of bromophenols was synthesized by reactions of corresponding phenol analogs with bromine. The synthesized compounds were tested for inhibitory activity against isocitrate lyase (ICL) of Candida albicans and antimicrobial activity against Gram-positive and, Gram-negative bacteria and fungi. Among the synthesized bromophenols, bis(3-bromo-4,5-dihydroxyphenyl)methanone (11) and (3-bromo-4,5-dihydroxyphenyl)(2,3-dibromo-4,5-dihydroxyphenyl)methanone (12) displayed potent inhibitory activities against ICL, showing a stronger inhibitory effects than were found with natural bromophenol 1. The preliminary structure-activity relationships were investigated in order to determine the essential structural requirements for the inhibitory activities of these compounds against ICL of C. albicans. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis and α-Glucosidase Inhibitory Mechanisms of Bis(2,3-dibromo-4,5-dihydroxybenzyl) Ether, a Potential Marine Bromophenol α-Glucosidase Inhibitor
  作者：Ming Liu、Wei Zhang、Jianteng Wei、Xiukun Lin

  DOI：10.3390/md9091554

  日期：——

  Bis(2,3-dibromo-4,5-dihydroxybenzyl) ether (BDDE), derived from the marine algae, is a potential α-glucosidase inhibitor for type 2 diabetes treatment. In the present study, a synthetic route was established as a valid approach to obtain BDDE. Fluorescence spectra, circular dichroism spectra and molecular docking methods were employed to elucidate the inhibitory mechanisms of BDDE against α-glucosidase. The results showed that BDDE could be prepared effectively and efficiently with the established synthetic methods. Synthetic BDDE bound with α-glucosidase and induced minor conformational changes of the enzyme. The docking results indicated the interaction between BDDE and α-glucosidase was driven by both hydrophobic forces and hydrogen bonds. The docked BDDE molecule was completely buried in the α-glucosidase binding pocket with part of the molecule reaching the catalytic center and overlapping with the position of glucose, and the rest of the molecule extending towards protein surface. This study provides useful information for the understanding of the BDDE-α-glucosidase interaction and for the development of novel α-glucosidase inhibitors.

  从海藻中提取的双（2,3-二溴-4,5-二羟基苄基）醚（BDDE）是一种潜在的α-葡萄糖苷酶抑制剂，可用于治疗 2 型糖尿病。在本研究中，建立了一条获得 BDDE 的有效合成路线。研究采用荧光光谱、圆二色光谱和分子对接等方法阐明了BDDE对α-葡萄糖苷酶的抑制机制。结果表明，利用已有的合成方法可以有效、高效地制备 BDDE。合成的BDDE与α-葡萄糖苷酶结合，并诱导该酶发生微小的构象变化。对接结果表明，BDDE 与 α-葡萄糖苷酶之间的相互作用是由疏水作用力和氢键共同驱动的。对接的BDDE分子完全埋藏在α-葡萄糖苷酶的结合袋中，部分分子到达催化中心并与葡萄糖的位置重叠，其余分子向蛋白质表面延伸。这项研究为了解 BDDE 与α-葡萄糖苷酶的相互作用以及开发新型α-葡萄糖苷酶抑制剂提供了有用的信息。